


Ultimate Win

by neosaiyanangel



Category: Kim Possible (Cartoon)
Genre: Anal Sex, Bad Ending, Dead Dove: Do Not Eat, Death by Anal Sex, Drug Use, Everyone is Dead, F/M, M/M, Non-Consensual Bondage, Noncon - Forced to have sex for entertainment of third party, Noncon - Rape is livestreamed, Noncon - Villain Forces Pining Couple to Fuck, PIV Sex, Rape, hopelessness
Language: English
Status: Completed
Published: 2020-04-27
Updated: 2020-04-27
Packaged: 2021-03-02 02:35:24
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Major Character Death, Rape/Non-Con, Underage
Chapters: 1
Words: 3,201
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23867623
Author URL: https://archiveofourown.org/users/neosaiyanangel/pseuds/neosaiyanangel
Summary: It was bound to happen eventually. Kim just expected to at least have a chance when it did happen.
Relationships: Dr. Drakken/Kim Possible, Dr. Drakken/Ron Stoppable, Kim Possible/Ron Stoppable
Comments: 4
Kudos: 10
Collections: Id Pro Quo 2020





	Ultimate Win

**Author's Note:**

  * For [Dirty_Lemon_Pit](https://archiveofourown.org/users/Dirty_Lemon_Pit/gifts).



> This is the most deviant thing I have ever written. No fluff or anything good in this. It is a hopeless painful fic that wrecks everything Kim loves. You have been warned!

"Uuuugh…" Kim came to consciousness slowly. Her head ached like it never had before and it felt like she was hanging by her arms in some shackles.

What in the world had happened? The last thing she remembered was going to bed after another family game night that she was once again the loser of. Nothing should have sparked this kind of groggy confusion.

She slowly and painfully opened her eyes. What she saw made them shoot straight open with a pang of pain.

Ron. He was in front of her wearing a set of boxers and nothing else. He looked to just be waking up himself, his eyelids hanging unevenly and gaze unfocused. She looked down and realized that she had been stripped down to her underwear.

What was going on?

"Oh good. You're awake."

The voice made Kim jerk her head to where it was coming from.

It was Drakken. He was wearing a bathrobe, a fuzzy blue thing, and apparently nothing else. That was really weird.

But…

There was something wrong. His skin looked darker and his eyes were violently bloodshot. He looked like he was sick, yet at the same time looked crazed. Even moreso than normal. And, she noted as she shot her head around, Shego was nowhere to be seen.

...Wait.

She looked around again. The room was circular and filled with some really weird stuff. Something that looked like a modified sawhorse, a rack, a table full of...sex toys?

A horrible sinking feeling filled her as she was connecting dots. She'd expected this to happen eventually, but Drakken? Kim almost felt betrayed. It was really unlike Drakken.

"So, you're trying out being insane or something? Trying to intimidate us?" Kim asked, trying to keep her heartbeat down.

"There's no 'try' about it." Drakken seemed to think for a moment. "Tell me, after the Lorwardians, did you still think I was evil?"

"No. You aren't really any kind of evil. More of a bully." Kim knew that would get under his skin.

Instead of growling and insisting he was a villain, he laughed and agreed, "You're right! I was hopeless. Completely and utterly hopeless."

Kim blinked. This was...very unlike Drakken. The sinking feeling got worse as she watched him carefully.

"Oh yes. I realized that I was one hundred percent the laughingstock of the world. 'See that Drakken? He's just a softy in disguise!' 'Drakken? Oh yes, he's such a good man!' 'My Drewbie! A hero!'" He spat. "Lot of fools, all of them!" His eye twitched. "No, I'm not a good man. I needed a spark, though, to bring it all back. To show everyone that I'm a villain!" He giggled. "Which is why I got my hands on an Attitudinator."

Kim gasped, horrified. "You used one?! After that mess with Zorpox?"

"Why not? It made the doofus into a semi-decent villain. Why wouldn't it make a slightly pathetic villain even better? And yes, I do believe it worked." He tilted his head. "I've had ideas. Ideas that would horrify most people. Ideas that would have horrified me before I Attitudinated myself. It let me know that it's worked, and that the plans I have from it will work too."

"You can't beat us!" Ron said, wrestling around with his chains. "You've never beaten us before, you can't beat us now even being super eviled up!"

Drakken, again, laughed. "If you were trying you probably could." His smile twisted. "But you won't want to. You'll want to do what I say."

"Yeah? Why would we do that?" Ron dared.

"No reason, really. Nothing beyond this." Drakken snapped his fingers.

Kim now took notice of a set of windows to her right. They flared light as the room beyond it lit up. She took in the scene and gasped.

Their families. Mom, Dad, Ron's parents, the tweebs...they were all shackled to tables, presented to the two teenagers like prized specimens. Rufus was in there, too, his entire body encompassed in metal with his head stuck in a little guillotine.

"Now then, Kim Possible and her doofus sidekick. If you don't play by my rules, your families will pay the price."

"What kind of price? Wholesale?" Ron asked curiously, clearly not reading the room.

Drakken sneered. "Just for that little quip, your 'little buddy' will be the demonstration." He shouted, "Naked weasel, the end!"

Kim watched, horrified, as the guillotine blade dropped. Rufus' head came neatly off, falling to the table with a couple of bounces. His mouth was opened and moving in a silent scream as the life dimmed and died in his eyes.

Ron simply...stared. He was staring blankly at the now lifeless body of his naked mole rat. "KP…" he said weakly. "KP, we're dreaming, right? Rufus didn't just die, did he?"

Kim couldn't answer. Her mouth was dry. She'd had villains try to kill her and her friends before, but those attempts were clownish at best. This? This was plain old monstrous.

"You killed him…" she managed to choke out.

"Yes, yes I did, didn't I?" Drakken sounded quite pleased with himself. "The rest of them are up on the chopping block...if you don't behave."

"What do you want?" The taste of defeat was bitter on Kim's throat. Combining that with what was around them...this was going to be a very bad time.

"I want you humiliated. I want to see you begging for the end. I want you to hurt." The words were intense and heartfelt. "You'll be all those things and more by the end of this. The only question is how many of your family members will be left by the end.

"Now then…" Drakken snapped his fingers again. The shackles holding Kim and Ron released, dropping them to the ground. Kim rolled to her feet while Ron landed hard on his butt. The villain eased himself into a chair and waved at them. "I want you two to have sex. Right here, right now."

Ron laughed uneasily. "Yeah, uhm. I have performance anxiety?"

Drakken frowned, then shouted, "Gene Stoppable, right arm!"

A flash of panic flew across Ron's face. "Wait! I was joking! Please—"

"Too late," Drakken noted, his gaze flickering to the window. Against her own desires Kim also looked.

A saw had dropped from the ceiling and had gotten to work on Ron's father's right arm. The short man was screaming and flailing, his right arm tensing before slacking as it came loose from his shoulder. The blood was gushing, and Kim was certain that he was going to die.

"I'm not up for your 'jokes'. I want what I want, and if I don't get what I want...well, you've seen what happens." Drakken tilted his head. "So? Are you going to keep me waiting?"

"How can we have sex when we're not even worked up?" Kim defended.

Drakken got up from his seat and Kim was certain that he had been hoping she would say that.

"Here." From his bathrobe he pulled out a syringe. "A bit of a booster for men."

"What about KP?"

"What about her? Be glad I'm helping out as it is!" Drakken barked, tossing the syringe at Ron. He resumed sitting and watching the two of them.

Kim said, "Ron? Are you sure you want to trust him? We could"

"I don't want to make him upset," Ron answered. "I, I don't want to lose anyone...else…" He swallowed hard before sticking the needle into his leg.

"It doesn't go there," Drakken interrupted before Ron could depress the plunger.

"What? Then where does it go?" Ron asked.

Drakken smirked.

"...oh." Ron got it just as Kim did. "Like...that's…"

"It's either that or your mother next~" Drakken sing-songed.

"Okay okay!" Ron tentatively, trying to hide himself from their family, pulled his boxers off. He winced as he inserted the needle into the base of his penis and injected it.

Kim watched him, waiting and hoping it wasn't secretly some kind of poison. But even if it was, did they really have a choice.

Ron shuddered and murmured, "Oh. Uh. I don't feel so good."

"It's not supposed to feel good," Drakken replied. "It's supposed to give you an erection."

Ron swayed for a few moments. Kim grabbed him to help hold him up. He leaned heavily against her. The only grim good thing about it was that Ron was, indeed, getting an erection. It looked red and very unlike what Kim ever thought it would, or should, look like. It was almost like he had a rubber band at the base of his penis.

"Oh look! It worked." Drakken lounged backwards. "Fuck Kimberly Anne now."

Ron was sweating, panting in pain, but he nodded. Swallowing, Ron murmured, "You, ah, ready, KP?"

Kim tensed before stiffly nodding. "Yeah. Uhm…" Like a robot, she removed what little clothes she had on.

The two of them stood there, staring at one another. They'd seen bits and pieces of each other naked, but never the whole picture.

"Hurry up!" Drakken snapped. "Your families don't have all day."

That made Kim look over to the window. Ron's father had stopped moving. At least his mother and Hana were still alive. Selfishly, she was glad it was Ron's family and not hers. She still had everyone. For now.

"Ron." She cradled his pinched face. "It's okay. We'll get through this."

Ron nodded again. "Yeah...it's, it's no big."

Kim stiltedly led him to the table covered in toys. She didn't know what even half of them were for. It made her worried about what would be coming next.

Desperately hoping the window was one-way, Kim climbed onto the table and rolled over. Ron paused, looking at her nervously. Kim sighed as she said, "Go ahead, Ron. I'll be fine."

Ron lined himself up with Kim and pushed hard into her. Kim winced; she wasn't wet at all. It hurt and was intrusive all at once. Shots of panic raced through her at the feelings, panic that she fought hard to keep down.

Ron was grunting in pain, tears biting at his eyes. He was clearly forcing himself to do everything as he pushed in and out slowly. He bent over and kissed Kim on the lips. A very half-hearted attempt to try and get Kim worked up.

A chuckle made her look over to Drakken.

Drakken sat in his chair, stroking his cock and grinning like the monster he was. Kim was trying hard, so hard, to not give in to his desire for her to break. Yes, her and Ron's first time was now ruined and they were putting on a sick show for him, but that didn't mean they should give up!

"Ah ah ah, Kimberly Anne! I see that rebellious little sparkle in your eye," Drakken said, waving a finger back and forth. "We can't have that." He shouted, "Anne Possible, left ankle!"

Kim froze in horror, willing herself not to look. She stared at Ron's face instead. Ron, who was also trying not to look and staring right back at Kim. The fear on his face echoed her heart.

Desperate to not lose anything or anyone else, Kim pulled Ron close. "Keep, ugh, going. I don't matter right now."

"I'm, so sorry, KP." Ron stopped in his half-hearted thrusting to let loose a few tears. "I can't believe this is happening…"

"I believe in you. You can, hnn, do this." Kim hooked her legs around Ron's middle. "Please."

"Right." Ron began to earnestly attempt to get Kim off. He was licking one of her nipples while pushing himself in and out of her. One of Kim's hands traveled down to her clit. She tried to work herself up while ignoring everything around them. All that mattered was herself and Ron.

She was finally wetting up, Ron's thrusts feeling good if manic. Kim looked up at him and, for the first time since all this started, felt like things would be okay.

"Bah! This is becoming so romantic I'm about to puke." Drakken shoved Ron off of Kim. Vines burst from under Drakken's robes and wrapped around Kim. She squawked in offense as she found herself tied down against the table. Drakken looked between the two of them. "You ripped the fun right out of that. It's time for me to get into the mix." He grabbed Ron's shoulder and pushed him to his knees. "Suck me off."

Ron flushed a brilliant red. "What?! You, you mean suck on your penis!?"

"Yes," Drakken said irritably. "Do it. Now. Or…" A positively nasty grin crossed his face. "Ohhh, that's a much better idea! You're rather smart sometimes, boy whose name I don't remember." Another set of vines shot out from Drakken's robes. "Go to the sex bench."

Kim bet Ron guessed what that was as he hesitantly made his way over to the sawhorse. Drakken pushed Ron into it with his ass hanging over the edge. Drakken's vines wrapped tight around him, tying him in place.

"Good." Drakken let out a manic giggle. "Now, I'll need to clean you out before I stick my dick anywhere near there."

"Clean me out?" Ron froze. "Wait. Are you gonna shove your you-know-what in my butt?!"

"You're such a child! It's a penis! And yes, I am!" Drakken had picked up one of the toys that were on the table next to Kim. It looked like a balloon attached to a hose of some sort. The villain strolled back over to Ron and unceremoniously shoved the hose up Ron's ass. Ron gasped and whimpered in pain, then made a strange strangled noise as Drakken pumped the balloon. "I'm not about to shove myself into a filthy asshole." Drakken did something weird with the little device that seemed to suck everything back into the balloon. "There! Should be nice and shiny clean."

"Oh, that did not feel good."

Drakken rolled his eyes. "Once again, this is not about you feeling good. Oh no. This is about me feeling good. And…" He suddenly looked thrilled as he seemed to remember something. "I do believe I forgot something!" He laughed. "I'm livestreaming this."

Chills ran through Kim. "...What?"

"Oh yes. This is being broadcast aroooooound the globe. For everyone to see!" Drakken twirled around. "Everyone watching Kim Possible being brought low by Dr. Drakken! How spectacular is that?"

Kim struggled against the vines, feeling very violated. Forcing her and Ron to have sex was one thing. Even having sex with them, while worse, was still tolerable. But to have everyone watching them? Their humiliation? The horror? How many people were getting off, watching them experience the worst day of their lives? She couldn't even cover herself. She was left bare for the home audience to oogle at.

"AH!" Her attention was brought back to Ron and Drakken as Drakken shoved himself into Ron. Drakken's gaze was solidly on Kim as he pushed hard into her boyfriend. The perverse enjoyment in his eyes made Kim wish she could punch him. Hurt him. Do something to make him pay.

But she could do nothing. She was helpless against the vines, stuck watching Ron be violated over and over. Drakken was relentlessly thrusting into Ron. Ron was crying in pain, flailing against the vines to no avail. Kim tried not to look once she saw blood starting to flow out of Ron's ass.

It was sick. It was all so sick!

"Looks like you're spent," Drakken murmured grumpily. She looked back over to see Ron laying limply against the sawhorse. Fear shot through her as Drakken looked back over to her. "Looks like it's your turn."

Kim struggled again, willing the vines to break as Drakken bore down on her. This was so wrong. She was a hero! This wasn't supposed to happen to her. Ron was one thing, but being violated by Drakken? On camera? She couldn't handle it.

She felt his penis brush against her vulva. "Hm. You're wet. How unfortunate. Oh well." Her teeth ground hard as Drakken pushed into her. He was thicker than Ron, a detriment. Drakken leaned over her and looked her straight in the eyes. "Are you scared yet, Kim Possible?"

Kim put on a brave face and spat out, "You wish, Drakken!"

"James Possible, the end." He said it slowly, deliberately, clearly enjoying her expression turn to horror.

This time she couldn't help but to look. Kim looked over just in time for a saw to neatly slice off her father's head. She began crying then, seeing her father dead and her mother missing a foot. The tweebs were crying and struggling to no success. Her mother was limp, probably from shock, while Ron's mother was simply staring at her husband's dead body.

"Yessss. This is what I wanted." Kim pulled away as Drakken brushed his hand across her cheek. "Your fear is what I wanted this entire time. It's so satisfying…! Hngh!" Disgust washed over her as Drakken came inside her. He gripped her shoulders tight as his orgasm hit him. It was torture, knowing that she was being filled by him.

Finally, thankfully, it was over. Drakken was gasping over her, his sweat dripping off his chin onto her chest. She shivered, a desperate beg on the tip of her tongue to end it all. Hopefully, now that he got what he wanted, this would all be done.

A dry chuckle from Drakken wiped that hope away. He looked back at her and she knew nothing was going to be okay.

"Yes," he whispered. "Feel that despair. Know that your life is ruined." He pulled out of her and shouted, "Game over!"

Kim was confused for a moment before she saw a set of saws drop from the ceiling in the other room. One for each person. She ducked her head away but found it forced back by Drakken's hands pressing her head to the table. Numbness flooded her as the heads popped off of each of them.

Jim.

Tim.

Mom.

Hana.

Mrs. Stoppable.

All of their heads went rolling, their bodies slumping against the restraints.

"I. Win." Drakken let Kim's head loose before standing fully up. "I feel rather refreshed!"

Kim couldn't bring herself to move.

Drakken walked over to Ron and poked him a few times. "Looks like he died. Probably from the drugs he took. I always knew that's how he would go out." He paused, thinking for a moment. "Or maybe blood loss. I ripped his ass pretty good." A sigh escaped his lips as he murmured, "I think I need a shower. I'll be back for round 2 shortly~" He practically danced out the door to the room, leaving Kim tied to the table.

She laid there for a while. Her family was dead. Ron's family was dead. Their humiliation had been broadcast to the entire world. And Ron might be dead, too.

"Ron?" she managed to squeak out. "Ron, are you okay?"

Everything was silent. She listened intently, hoping to hear him breathing.

There was nothing.

Somehow, Kim found more tears as her eyes dripped her misery.

Drakken had won.


End file.
